Florida's Highwaymen Painted Idealized Landscapes In Jim Crow South

And if you're just joining us, this is WEEKENDS on ALL THINGS CONSIDERED from NPR News. I'm Jacki Lyden.

In the winter of 2012, I came across a story on a drive through central coastal Florida in the town of Fort Pierce. Route 1 is now dominated by strip malls and fading condos, but the Florida of the 1950s and '60s was a candy-colored Eisenhower, Kennedy space-age dream of flaming red Poinciana trees and untamed beaches.

This setting gave way to the improbable rise of The Highwaymen, young African-American painters making their fortunes in the Jim Crow South. The paintings are boldly colored landscapes depicting scenes that used to be common in this part of Florida: moss-draped live oaks hanging over moonlit river inlets, delicate white egrets flying across a brilliant orange sunset, palm trees that arch like sabers over the ocean, all painted by The Highwaymen on boards made of leftover construction material and all sold by the group's smooth-talking salesman Al Black.

AL BLACK: Good morning. So my name is Al Black. I have some oil paintings. I want to know would you all be interested if it wouldn't take up too much of yous time?

LYDEN: With that pitch, 50 years ago, Al Black would troll up and down U.S. 1 looking sharp, driving a 1962 blue and white Ford Galaxy, fresh Florida landscapes packed in his trunk.

BLACK: And most of the time, there was a, yes, I'll look. And once they look, I would sell them something.

LYDEN: They sell for thousands now. They're collectors' items owned by celebrities like Shaquille O'Neal and Steven Spielberg. Highwaymen paintings hang in the Florida State House and at the White House. The man who started it all was a teenage artist named Alfred Hair.

JAMES GIBSON: Alfred was a small dude.

LYDEN: James Gibson, Alfred Hair's best friend and fellow painter.

GIBSON: He could paint fast. People were buying the paintings real fast. He would sell a painting like 19 and $20. You could paint four or five paintings in a day. That's $100 a day. But you got the - go and sell your paintings.

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LYDEN: Back in the '60s, Alfred Hair, a charismatic and talented high school student from a good family was taken by his art teacher across the railroad tracks, literally the color line in Fort Pierce, to see a famous local artist and humanitarian named A.E. Beanie Backus.

GIBSON: Alfred had gone down to Mr. Backus. Mr. Backus was a famous white artist.

LYDEN: James Gibson remembers it this way.

GIBSON: At this particular time, his door was open to anybody who was interested in art - black, whatever, white, anybody. And if you're interested, he'll be your teacher. And so what happened, after showing his first painting, then he wrote and told me, James, I went to Mr. Backus and he taught me how to paint. And if I did it, I know you can do it.

LYDEN: They were making money and happy to show it at the dog track, on fancy cars, on women. No one lived like the Highwaymen. There was envy from other men. One night, it came to a head at a juke joint called Eddie's Place.

BLACK: Me and him went out, and he said, meet me down at Eddie's Place.

LYDEN: The events of that night have become as epic as a blues song. All the Highwaymen tell slightly different versions of what happened. Al Black, Alfred's top salesman, claims he was at Eddie's that night.

BLACK: When we took him to the hospital. I was the onliest one standing by the bed when he died.

GIBSON: I am the one that talked to Alfred last.

LYDEN: Artist James Gibson.

GIBSON: He was trying to tell me something, and I put my ear, then Dr. Goulds(ph) came in and said that Alfred Hair's retired.

LYDEN: When Alfred Hair died, the enterprise of the Highwaymen nearly died with him. Demand dwindled. By the '90s, the painters had all but stopped, which left their salesman, Al Black, with no paintings to sell. He started making his own, but that led to other problems.

BLACK: That's right. You can have foot trouble, back trouble, neck trouble, all kind of trouble. You ain't had no trouble till you had some crack cocaine trouble.

LYDEN: He was caught up in drug addiction and was accused of fraud. Al Black ended up in prison where he'd spent 12 years transforming the walls of various state penitentiaries with his landscape murals. The other Highwaymen had families, careers, moved out of state, but James Gibson kept painting prolifically. Lucky for us, he showed us his paintings the old-fashioned way, under a tree in a park, pulling them out of the trunk of his white Cadillac Escalade. Wow.

GIBSON: This the main groves. This is...

LYDEN: Ooh, look at that.

GIBSON: You got all the brilliant colors - bright orange, yellow. When it get cold, you look at this color, and it'll warm you up mentally.

LYDEN: Oh, that is really lovely.

If you want yellow, Gibson will paint it for you in yellow or blue or orange. The Highwaymen have come a long way since the days of their first efforts. A book written about them in 2001 brought them once more before the public eye. They've been honored by the Florida Hall of Fame and have been admired by some big collectors. Others still live precariously.

As he prepared for an art festival in far away Tallahassee, we visited Al Black in Fort Pierce in the paint-splattered tent that serves as his backyard studio. Out of prison now for five years, he makes a living once more selling his own paintings. And he told us he hoped to finish six of them to bring with him to the festival. Sounds like a lot, but he already had four going at once.

BLACK: This is going to be a backwood marsh scene. This is going to be a moonlight in the Indian River. And this is going to be down at the dock where they put the boats in the water.

LYDEN: Today, Al Black is one of the few Highwaymen artists who still paints this way - outdoors, several canvasses at a time. It's this kind of assembly line technique that makes some people question whether this is really art. Al Black is certain it is.

BLACK: See, for instance, these paintings, what I'm painting on right now, these are some good paintings because I'm putting my heart into them.

LYDEN: To see a video of Al Black and hear that sales pitch, please go to our website, npr.org. Our thanks go to videographer Dave Anderson of Southword and the Oxford American magazine. And a special thanks to photographer Gary Monroe, who documented the Highwaymen and books, and his photos are featured on NPR's Picture Show blog. And a big thanks to the producer Liz Baker, who was a great sidekick out on the road. Transcript provided by NPR, Copyright NPR.